How to Thrive in an Unstructured Environment

“Perfect is the enemy of done.” No experience has helped me internalize this more than my summer at blueground, an international, vc-backed real estate startup. Before business school, I worked at a large oil & gas company, where structure and process were integral to operations, yet nimbleness and ingenuity was still highly valued. I loved working in an environment that combined these elements, and I wanted to take a deep dive into the chaotic world of startups to see if I could thrive in an environment with significantly less structure.

I chose blueground because it gave me the opportunity to work on a “startup” within a startup. Almost at 180 people now, blueground offers fully furnished, elegant apartments for travelers looking to stay for at least a month at a time. My summer role was to work with one of the co-founders based out of New York City to build out blueground’s global corporate sales strategy.

Throughout this experience, I worked on everything from “blue sky” brainstorming sessions and developing strategies, to attending conferences, implementing new software systems, and designing marketing materials. Below are three of key lessons I’ve gained from this incredible learning opportunity.

1. Have a north star. Recalibrate towards it daily.

Before this internship, I chatted with an HBS professor with enterprise sales expertise to come up with a tentative game plan for the summer. Through this conversation, I recognized that I would be spending the summer learning and implementing at the same time. Yet, I was itching to create a summer work plan with weekly objectives.

However, as my internship progressed, I realized that creating a plan for the entire summer would have been futile. Every day, we learned something new that helped us make better decisions and shaped our path forward. Now, towards the end of the summer, we are finally armed with enough information and experience to create a weekly and monthly plan.

I learned that when you’re in the very early discovery and learning stages, it’s better to simply outline your two or three big goals and let those function as your north star. Every morning, look at your to-do list. Throw out the action items that may no longer be relevant given the new information you learned from the day prior. See how your remaining desired activities align to your big goals. Your plan will always be changing, and that’s how you know you’re learning!

2. You cannot learn without making mistakes.

Developing a new business idea requires you to learn as fast as possible. Research is important, but it’s easy to paralyze yourself by spending too much time analyzing the options. At some point, you need to enter execution mode and test the options to learn.

For example, when I was researching the sales prospecting process, there were many software systems to choose from. Rather than spend weeks, even days, researching between them, we tested two different systems that were recommended to us, tested the pros and cons in real time, and picked the one that worked best for us. You want to expedite the virtuous cycle of trying, learning, and adapting.

3. Surround yourself with the best resources: people.

Books, blogs, and articles are great places to learn the building blocks of a new process, but they only get you so far. The best resources are truly other people - the people who have achieved what you’re looking to do before or are currently in the weeds now. Leveraging our personal network and LinkedIn, we spoke to individuals almost weekly that have enterprise sales expertise such as B2B founders, sales startup consultants and Sales Development Representatives at other startups. Every conversation enabled us to learn from their process and best practices uncovering one piece of the puzzle at a time. This collective feedback was pivotal in enabling us to accelerate our learning process and begin implementing our strategy.

Overall, this summer has been an incredible learning opportunity to experience a new industry, function, and city! I’m looking forward to bringing these lessons back with me to share in my entrepreneurship classes in the Fall and to my future career opportunities post HBS.